D. Reger, James R. Gardinier, P. Pellechia
Nov 17, 2003
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16
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Journal
Inorganic Chemistry
Abstract
The reaction between (1-acetyl)pyrene and dimethylformamide dimethylacetal followed by condensation of the resulting product mixture with hydrazine affords 3(5)-(1-pyrenyl)pyrazole (2) in good yield. The easily separable bis[(1-pyrenyl)pyrazole]methane derivatives CH2(3-pzpyrene)2 (3a, pz = pyrazolyl ring) and CH2(3-pzpyrene)(5-pzpyrene) (3b) were prepared by metathetical reactions between pyrazole and CH2Cl2, while CH(nPr)(pzpyrene)2 (4) was prepared by transamination of 2 with butyraldehyde diethylacetal. Compounds 2−4 are luminescent under irradiation with UV light and have pyrenyl monomer-based emissions centered near 400 nm. Compounds 3a and 4 each react with Re(CO)5Br in a 1:1 molar ratio to form highly insoluble complexes Re(CO)3Br[(pzpyrene)2CH2] (5) and Re(CO)3Br[(pzpyrene)2CH(nPr)] (6). Complex Re(CO)3Br[(pz)2CMe2] (7) was also prepared. X-ray structural studies of 6 show extensive π-stacking of pyrenyl groups to form two-dimensional sheets. Pulsed field gradient spin−echo NMR (PGSE-NMR) experim...